Cage opening of parent closo cage carboranes with fluoride ion: formation of 5-fluoro-hexahydro-nido-2,4-dicarbahexaborate(1-) ([5-F-nido-2,4-C2B4H6]-)

Tomita, Harumi.; Luu, Helen; Onak, Thomas

doi:10.1021/ic00004a038

Cited by 76 publications

(19 citation statements)

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“…[11a] These include selective substitution of the hydrogen atom of boron atom B9 [29] or deboronation of the closo cluster to give nido derivatives. [30] Preliminary NMR spectroscopic studies have shown that 2 b reacts with tetra-n-butylammonium fluoride (TBAF) in THF at room temperature to form the corresponding nido species without PÀP bond cleavage. The resulting nido cluster should be an interesting ligand in transition metal chemistry because it combines the features of a nido-carbaborane ligand with those of an oligophosphane.…”

Section: Discussionmentioning

confidence: 99%

Carbaborane‐Substituted 1,2,3‐Triphospholanes and 1‐Aza‐2,5‐diphospholane: New Synthetic Approaches

Kreienbrink

Heinicke

Pham

et al. 2013

Chemistry A European J

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Section: Discussionmentioning

confidence: 99%

Carbaborane‐Substituted 1,2,3‐Triphospholanes and 1‐Aza‐2,5‐diphospholane: New Synthetic Approaches

Kreienbrink

Heinicke

Pham

et al. 2013

Chemistry A European J

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“…In turn, a wide range of carborane derivatives may be synthesized regioselectively without the need for complex protecting groups. Bases, such as pyrrolidine or fluoride, may be used to generate nido-carboranes 4, 5, and 6 (Figure 1) [17][18][19][20][21]. Such reactions convert the extremely hydrophobic closo-carboranes to the hydrophilic nido-carboranes [22][23][24].…”

Section: Estrogen Receptormentioning

confidence: 99%

The Use of Carboranes in Cancer Drug Development

O¹,

Mason²,

Lee³

2019

Int J Cancer Clin Res

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Over the past decade, there has been a rising interest in the use of carboranes as a potential pharmacophoric moiety in the development of new drugs for the treatment of various types of cancer. The unique physical and chemical properties of carboranes make their use attractive in drug development. In several instances, the inclusion of carboranes into a drug structure has increased the agent's binding affinity, potency, or bioavailability. The purpose of this review is to highlight applications of carboranes to the medicinal chemistry of cancer. erwise rapidly metabolize [5]. Furthermore, selective chemical substitution of each carbon or boron atom in these clusters allows for their use as rigid, three dimensional scaffolds upon which to construct new drug molecules.Nearly all past biomedical research involving carboranes has focused on their use in the design of boron delivery agents for boron neutron capture therapy (BNCT)[2]. This binary radiation therapy depends on the selective delivery of a high concentration of boron-10 atoms to targeted tissues. It is generally accepted that a minimum concentration of 30 ppm is required for successful BNCT therapy and this concentration is equivalent to the delivery of approximately 10 9 boron atoms to each targeted cell. As BNCT human clinical trials have been attempted nearly continuously for the past five decades, there is a large body of literature associated with the use of carboranes for the development of BNCT boron agents. There are several good reviews and books covering that work [6][7][8][9][10][11][12][13]. While BNCT requires the delivery of large quantities of boron to diseased tissue, (requiring concentrations of boron in the low millimolar range) there is an increasing interest to use carboranes to synthesize new and highly potent drugs which operate at the opposite extreme of the concentration range, namely nanomolar, to picomolar.Ortho-carborane and its carbon-functionalized derivatives may be prepared by reacting acetylene (or functionalized acetylene) with the decaborane derivative B 10 H 12 L 2 , where L is a weak Lewis base [3,14]. The acetylenes used in these reactions include a wide range of functional groups such as esters, halides, carbamates, ethers, and nitro groups; however, such reactions are not successful in the presence of

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“…Towards making the precursor needed for radiolabeling, a 1 H NMR study was performed to evaluate the reactivity of 7 towards formation of the nido-carborane 8. The conventional method to remove a BH vertex is treatment of closo-ortho-carboranes with a strong base [71][72][73], which could degrade the tetrazine. However, the electron withdrawing nature of the amide linkage should facilitate deboronation under milder conditions [25].…”

Section: A C C E P T E D Accepted Manuscriptmentioning

confidence: 99%

Synthesis, characterization and radiolabeling of carborane-functionalized tetrazines for use in inverse electron demand Diels–Alder ligation reactions

Genady

Tan

El‐Zaria

et al. 2015

Journal of Organometallic Chemistry

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Cage opening of parent closo cage carboranes with fluoride ion: formation of 5-fluoro-hexahydro-nido-2,4-dicarbahexaborate(1-) ([5-F-nido-2,4-C2B4H6]-)

Cited by 76 publications

References 3 publications

Carbaborane‐Substituted 1,2,3‐Triphospholanes and 1‐Aza‐2,5‐diphospholane: New Synthetic Approaches

Carbaborane‐Substituted 1,2,3‐Triphospholanes and 1‐Aza‐2,5‐diphospholane: New Synthetic Approaches

The Use of Carboranes in Cancer Drug Development

Synthesis, characterization and radiolabeling of carborane-functionalized tetrazines for use in inverse electron demand Diels–Alder ligation reactions

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